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Maisha Riddlesprigger currently serves as the Head of Academics at Overtime, a position held since June 2021, while also holding a long-term role at the District of Columbia Public Schools (DCPS) since June 2009, where responsibilities have included both Principal and Assistant Principal roles. Previous experience includes serving as the Coordinator of Recruiting Services at Compton Unified School District from February 2005 to June 2009 and as an Adjunct Professor at Pepperdine University in 2006, teaching Math Methods for Elementary School Teachers. Prior to these roles, Maisha Riddlesprigger worked as a Content Seminar Manager at The New Teacher Project from 2003 to 2005 and began career as a Teacher at Compton Unified School District from 2000 to 2003. Education credentials include a BA in Psychology with an Education Minor from the University of California, Los Angeles, obtained from 1996 to 2000, and a MA in Education Administration from California State University-Long Beach, completed from 2004 to 2006.